Synthesis of (Hetaryl)alkylamines from the Reactions of 2‐Aminopyrimidine, 2‐Aminothiazole, and 2‐Aminothiazoline with Benzyl Bromide and Xylylene Dibromides

Abstract

Alkylation reactions of 2‐aminopyrimidine, 2‐aminothiazole, 2‐aminothiazoline, and their Cbz‐protected derivatives are described. Reactions with benzyl bromide proceed to give monoalkylated products with 2‐aminopyrimidine and 2‐aminothiazole, but 2‐aminothiazoline gives a dialkylated product. Reactions with xylylene dibromides are complicated by the tendency to form intramolecularly cyclized products with the ortho‐dibromide and insoluble products with the meta‐ and para‐dibromides.

Keywords:

• amine
• heteroaromatic
• pyrimidine
• thiazole
• thiazoline

Acknowledgments

The authors thank the Robert A. Welch Foundation (N‐1375) for support of this research.